Conductive die attach composition

Abstract

The present invention A resin containing one or more maleimide, itaconimide, or nadiimide functional groups, or a combination of the said functional groups. Epoxy components, (meth)acrylate component, Aromatic anhydrides, and conductive filler, The present invention provides a conductive die attach composition containing the following:

Description

[Technical Field]

[0001] The present invention (a) A resin containing one or more maleimide, itaconimide, or nadiimide functional groups, or a combination of the said functional groups. (b) Epoxy components, (c)(meth)acrylate component, (d) aromatic anhydride, and (e) Conductive filler, The present invention provides a conductive die attach composition containing the following: [Background technology]

[0002] For semiconductor device designers and manufacturers, package reliability is one of the most challenging factors. One reason for this is that copper, nickel, and nickel alloys, which are widely used as lead frame materials in the industry today, have problems with adhesive instability, especially under harsh environmental conditions.

[0003] These metals and metal alloys are used in lead frame structures because they possess a high coefficient of thermal expansion (CTE), high heat dissipation, and high thermal conductivity. However, due to the aforementioned adhesion instability, improving the adhesion of die attach paste to copper, nickel, and nickel alloy lead frames has been a long-desired but unfulfilled challenge. While efforts have been made to overcome the shortcomings of existing die attach materials, achieving consistent performance across die attach materials has been difficult until now. [Overview of the Initiative] [Means for solving the problem]

[0004] The present invention (a) A resin containing one or more maleimide, itaconimide, or nadiimide functional groups, or a combination of the said functional groups. (b) Epoxy components, (c)(meth)acrylate component, (d) aromatic anhydride, and (e) Conductive filler, The present invention provides a conductive die attach composition containing the following:

[0005] When the conductive die attach composition is cured by exposure to high-temperature conditions, it exhibits a die shear strength against a copper lead frame exceeding approximately 200% by weight compared to a comparative composition without aromatic anhydrides, even after further exposure to high-temperature conditions of approximately 85°C to approximately 125°C, for example, approximately 121°C, and high humidity conditions of approximately 85% to approximately 100% for approximately 16 hours. In other words, the adhesion between the substrate and the die attach paste is less likely to be broken even when exposed to such conditions. Furthermore, the conductive die attach composition also contributes to improved solder reflowability. [Modes for carrying out the invention]

[0006] As described above, the present invention is (a) A resin containing one or more maleimide, itaconimide, or nadiimide functional groups, or a combination of the said functional groups. (b) Epoxy components, (c)(meth)acrylate component, (d) aromatic anhydride, and (e) Conductive filler, The present invention provides a conductive die attach composition containing the following:

[0007] resin The resin (a) used in the conductive die attach composition of the present invention may be selected from one or more of the following:

[0008] [ka]

[0009] During the ceremony, m=1~15, R is independently selected from hydrogen or alkyl groups having 1 to approximately 4 carbon atoms. X is a monovalent or polyvalent linkage containing an organic group or an organosiloxane group.

[0010] For example, more specific representations of maleimide, itaconimide, and nadiimide include those corresponding to structures I, II, and III, in which, m=1~6, R is independently selected from hydrogen or a lower alkyl group. X comprises a monovalent or polyvalent linkage selected from linear or branched alkyl, alkylene, oxyalkyl, oxyalkylene, alkenyl, alkenylene, oxyalkenyl, oxyalkenylene, ester, reverse ester, polyester, amide, reverse amide, or polyamide, optionally interrupted or substituted with one or more heteroatoms such as oxygen, nitrogen, and / or sulfur, and optionally functionalized with substituents selected from hydroxy, alkoxy, carboxy, nitrile, cycloalkyl, or cycloalkenyl, with the number of carbon atoms in the linkage being approximately 12 to approximately 500.

[0011] In a particularly preferred embodiment of the present invention, each maleimide, itaconimide, and / or nadiimide functional group in the maleimide, itaconimide, and / or nadiimide compound is bonded to a monovalent group, or the maleimide, itaconimide, and / or nadiimide functional groups in the maleimide, itaconimide, and / or nadiimide compound are separated by a polyvalent group, each monovalent or polyvalent group having sufficient length and branching to liquefy the maleimide and / or nadiimide compound.

[0012] In a more specific description of maleimides, itaconimides, and nadiimides of such structures I, II, and III, each R is independently hydrogen or an alkyl having 1 to about 4 carbon atoms, X includes branched alkyl, alkylene, or alkylene oxide species having sufficient length and branching to liquefy the maleimide, itaconimide, or nadiimide compound, and m is 1, 2, or 3.

[0013] Preferably, resin (a) may be phenylenedimaleimide (for example, commercially available from Arkema under the trademark name SR-525A, with a particle size of less than 10 μm according to the manufacturer).

[0014] Resin (a) may be present in an amount of about 1% to about 10% by weight, for example about 1% to about 3% by weight, based on the total weight of the composition.

[0015] Epoxy component The epoxy component (b) used in the conductive die attach composition of the present invention may be selected from an aromatic epoxy resin, an aliphatic epoxy resin, and an alicyclic epoxy resin. Of course, these epoxy resins may be used in combination.

[0016] More specifically, in the case of an aromatic epoxy resin, the epoxy component (b) may be selected from a biphenyl epoxy resin, a bisphenol A, E, S or F epoxy resin, and combinations thereof.

[0017] In the case of an aliphatic epoxy resin, the epoxy component is a monofunctional epoxy compound: C4-C 28 alkyl glycidyl ether; C2-C 28 alkyl- and alkenyl-glycidyl ester; C1-C 28Alkyl- and monophenol glycidyl ethers; and polyfunctional epoxy compounds: pyrocatechol, resorcinol, hydroquinone, 4,4′-dihydroxydiphenylmethane (or bisphenol F, e.g., RE-303-S or RE-404-S available from Nippon Kayaku (Japan)), 4,4′-dihydroxy-3,3-dimethyldiphenylmethane, 4,4′-dihydroxydiphenyldimethylmethane (or bisphenol A), 4,4′-dihydroxydiphenylmethylmethane, 4,4'-dihydroxydiphenylcyclohexane, 4,4-dihydroxy-3,3'-dimethyldiphenylpropane, 4,4'-dihydroxydiphenylsulfone, and polyglycidyl ethers of tris(4-hydroxyphenyl)methane; polyglycidyl ethers of transition metal complexes; chlorinated and brominated products of the above diphenols; polyglycidyl ethers of novolacs This may include: diglycidyl ethers; polyglycidyl ethers of diphenols obtained by esterifying diphenol ethers obtained by esterifying salts of aromatic hydrocarboxylic acids with dihaloalkanes or dihalogenated dialkyl ethers; polyglycidyl ethers of polyphenols obtained by condensing phenol with long-chain halogenated paraffins containing at least two halogen atoms; N,N'-diglycidyl-aniline; N,N'-dimethyl-N,N'-diglycidyl-4,4'-diaminodiphenylmethane; N,N,N',N'-tetraglycidyl-4,4-diaminodiphenylmethane; N,N'-diglycidyl-4-aminophenylglycidyl ether; N,N,N',N'-tetraglycidyl-1,3-propylenebis-4-aminobenzoate; phenol novolac epoxy resins; cresol novolac epoxy resins; and combinations thereof.Commercially available epoxys useful as epoxy components include polyglycidyl derivatives of phenol compounds, such as the Resolution Performance trademark EPON, e.g., EPON 1009F [Bisphenol A epoxy resin (CAS number 25036-25-3)], EPON 1001F, EPON 1002F, EPON 1004F, EPON 1007F, EPON 3001, EPON 3002, EPON 2002, EPON 2003, EPON 2004, EPON 2005, EPON N2012, Epon 2014, Epon 2024, and Epon 2042; Dow Chemical Company's trademark DER, e.g., DER331, DER332, DER383, DER354, and DER542; Huntsman Company's trademark Araldite, e.g., Araldite [phenol-4,4'-(1-methylethylidene)bis(chloromethyl)oxirane (CAS number 25068-38-6)], Araldite ECN1299 [formaldehyde, (chloromethyl )Oxirane and 2-methylphenol polymer, melting point 85-100°C (CAS number 29690-82-2)], and Araldite ECN1285 [formaldehyde, (chloromethyl)oxirane and 2-methylphenol polymer, melting point 80-90°C (CAS number 29690-82-2)], and Araldite CT7097US [(phenol, 4-(1,1-dimethylethyl), (chloromethyl)oxirane and 4,4-(1-(1-methyl Examples include ethylidene bis polymers (melting point 113-123°C (CAS number 67924-34-9)) and BREN-S from Nippon Kayaku (Japan). Other preferred epoxy resins include polyepoxides prepared from polyols and the like, and polyglycidyl derivatives of phenol-formaldehyde novolac, the latter of which are commercially available from Dow Chemical under the trademark DEN, e.g., DEN431, DEN438, and DEN439.

[0018] Polyglycidyl adducts of amines, amino alcohols, and polycarboxylic acids are also useful in the present invention. Examples of commercially available resins include BP Chemicals LTD's Glyamine 135, Glyamine 125, and Glyamine 115; and Huntsman's Araldite MY720, Araldite MY721, Araldite MY0500, and Araldite MY0510.

[0019] The epoxy component (b) may be present in an amount of about 0.5% to about 10% by weight, for example, about 1% to about 2% by weight, based on the total weight of the composition.

[0020] (meth)acrylate component The (meth)acrylate component (c) used in the conductive die-attach composition of the present invention may be selected from monofunctional (meth)acrylate, bifunctional (meth)acrylate, or polyfunctional (meth)acrylate, and may be a monomer, oligomer, or polymer.

[0021] If the (meth)acrylate component (c) is a monofunctional (meth)acrylate, then H2C=CGCO2R 1 It can be expressed as follows, where G is selected from H, halogens, and alkyls having 1 to about 4 carbon atoms, and R 1 The group is selected from alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkaryl, and aryl groups having 6 to about 16 carbon atoms, with or without substitution or interruption by a member selected from the group consisting of silane, silicon, oxygen, halogen, carbonyl, hydroxyl, ester, carboxylic acid, urea, urethane, carbamate, amine, amide, sulfur, sulfonate, and sulfone. A commercially available example of a monofunctional (meth)acrylate is Arkema's SR506A (isobornyl acrylate).

[0022] Therefore, difunctional (meth)acrylates or polyfunctional (meth)acrylates may have (meth)acrylate functional groups at their terminals or in a pendant-like manner along the chain or skeleton between terminals. Examples of commercially available polyfunctional (meth)acrylates include Arkema's SR368 (trifunctional acrylate) and / or SR248 (neopentyl glycol dimethacrylate), respectively.

[0023] Specific examples of (meth)acrylate component (c) include silicone (meth)acrylate, polyethylene glycol di(meth)acrylate, tetrahydrofuran (meth)acrylate and di(meth)acrylate, hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, isobornyl acrylate, hexanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylenediglycol di(meth)acrylate, diglycerol tetra(meth)acrylate, tetra You may select from lamethylene di(meth)acrylate, ethylene di(meth)acrylate, neopentyl glycol di(meth)acrylate, butanediol di(meth)acrylate, bisphenol-A-(meth)acrylate, ethoxylated bisphenol-A-(meth)acrylate, bisphenol-F-(meth)acrylate, ethoxylated bisphenol-F-(meth)acrylate, bisphenol-A di(meth)acrylate, ethoxylated bisphenol-A-di(meth)acrylate, bisphenol-F-di(meth)acrylate, and ethoxylated bisphenol-F-di(meth)acrylate.

[0024] The (meth)acrylate component (c) should be present in an amount of about 1% to about 30% by weight, for example, about 10% to about 20% by weight, based on the total weight of the composition.

[0025] aromatic anhydride The aromatic anhydride (d) used in the conductive die attach composition of the present invention may be a functionalized trimellitic anhydride, for example, the following 4-methacryloxyethyl trimellitic anhydride ("4-META"). [ka]

[0026] Aromatic anhydride (d) should be present in an amount of about 0.1% to about 1% by weight, for example, about 0.2% to about 0.8% by weight, based on the total weight of the composition.

[0027] Conductive filler The conductive filler (e) used in the conductive die attach composition of the present invention should be silver powder or silver flakes, but other conductive fillers may be used instead of silver or in addition to silver. Examples of such other conductive fillers include copper, gold, alumina, graphite, and the like.

[0028] The conductive filler (e) may, in some cases, be a combination of silver powder and silver flakes.

[0029] The particle size of the conductive filler (e) should be in the range of about 10 -7 ~ about 10 -6 . For example, the conductive filler (e) may be silver powder with a particle size of about 10 -6 or silver flakes with a particle size of about 10 -7 .

[0030] The conductive filler (e) should be present in an amount of about 10% to about 90% by weight, for example about 60% to about 80% by weight, based on the total weight of the composition.

[0031] Hardening agent In some embodiments, it may be desirable to include a hardening agent in the conductive die attach composition of the present invention.

[0032] Suitable hardening agents include heat-curing catalysts that lower the temperature at which curing occurs or accelerate the degree of curing when appropriate temperature conditions for curing are selected.

[0033] The heat-curing catalyst may be selected from free-radical catalysts, anionic hardening agents, cationic hardening agents, and combinations thereof.

[0034] For example, the free radical catalyst may be selected from peroxides, azo compounds, and combinations thereof. Particularly desirable peroxide catalysts include dicumyl peroxide, dibenzoyl peroxide, 2-butanone peroxide, tert-butyl perbenzoate, di-tert-butyl peroxide, 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane, bis(tert-butylperoxyisopropyl)benzene, and tert-butyl hydroperoxide. Examples of azo compounds include 2,2'-azobis(2-methylpropanenitrile), 2,2'-azobis(2-methylbutanenitrile), and 1,1'-azobis(cyclohexanecarbonilonitrile).

[0035] Commercially available examples of these free radical catalysts include those sold by AkzoNobel, such as the following peroxides: dl-isobutyryl peroxide (CAS No. 3437-84-1-), cumyl peroxyneodecanoate (CAS No. 26748-47-0), peroxydicarbonate mixture (CAS Nos. 105-64-6; 19910-65-7; 78350-78-4), 2,4,2-trimethylpentyl-2 peroxyneodecanoate (CAS No. 51240-95-0), cumyl peroxyneoheptanoate (CAS No. 68299-16-1), and di-sec-butyl peroxydicarbonate (CAS No. 19910 -65-7), tert-butylperoxyneodecanoate (CAS No. 26748-41-4), dibutylperoxydicarbonate (CAS No. 16215-49-9), dicetylperoxydicarbonate (CAS No. 26332-14-5), di(4-tert-butylcyclohexyl)peroxydicarbonate (CAS No. 15520,-11-3), di(2-ethylhexyl)peroxydicarbonate (CAS No. 16111-62-9), dimyristylperoxydicarbonate (CAS No. 5322 0-22-7), tert-butylperoxyneoheptanoate (CAS No. 26748-38-9), tert-amylperoxypivalate (CAS No. 29240-17-3), tert-butylperoxypivalate (CAS No. 927-07-1), di-(3,5,5-trimethylhexanoyl)peroxide (CAS No. 3851-87-4), dilauroyl peroxide (CAS No. 105-74-8), dioctanoyl peroxide (CAS No. 762-16-3), didecanoyl peroxide (CAS CAS No. 762-12-9), 2,5-dimethyl-2,5-di(2-ethylhexanoylperoxy)hexane (CAS No. 13052-09-0), tert-amylperoxy-2-ethylhexanoate (CAS No. 686-31-7), tert-butylperoxy-2-ethylhexanoate (CAS No. 3006-82-4), dibenzoyl peroxide (CAS No. 94-36-0), 1,1-di(tert-butylperoxy)-3,3,5-trimethylcyclohexane (CAS No. 6731-36-8), 2,2-Bis[4,4-di-(tert-butyl-peroxy-cyclohexylpropane] (CAS No. 1705-60-8), 1,1-di(tert-amylperoxy)cyclohexane (CAS No. 15667-10-4), 1,1-di(tert-butylperoxy)cyclohexane (CAS No. 3006-86-8), tert-amylperoxy 2-ethylhexyl carbonate (CAS No. 70833-40-8), tert-butylperoxy-3,5,5-trimethylhexanoate (CAS No. 13122-18-4), tert-butylperoxy-2-methylbenzoate (CAS No. 22313-62-8), 2,2-di-(tert-butylperoxy)butane (CAS No. 2167-23-9), 、tert-butylperoxyisopropyl carbonate (CAS No. 2372-21-6), tert-butylperoxy-2-ethylhexyl carbonate (CAS No. 34443-12-4), tert-amylperoxybenzoate (CAS No. 4511-39-1), tert-butylperoxyacetate (CAS No. 107-71-1), butyl 4,4-di-(tert-butylperoxy)valerate (CAS No. 995-33-5), tert-butylperoxy Nzoate (CAS No. 614-45-9), di-tert-amyl peroxide (CAS No. 10508-09-5), dicumyl peroxide (CAS No. 80-43-3), di-(tert-butylperoxyisopropyl)benzene (CAS No. 25155-25-3), 2,5-dimethyl-2,5-di(tert-butylperoxy)hexane (CAS No. 78-63-7), tert-butylcumyl peroxide (CAS No. 3457-61-2), 2,5-dimethyl-2, 5-Di(tert-butylperoxy)hexyn-3 (CAS No. 1068-2-7-5), Di-tert-butylperoxide (CAS No. 110-05-4), 3,6,9-Triethyl-3,6,9-Trimethyl-1,4,7-Tripeloxonane (CAS No. 24748-23-0), 1,1,3,3-Tetramethylbutylhydroperoxide (CAS No. 5809-08-5), Diisopropylbenzene monohydroperoxide (CAS No. 26762-93-6), Kumilch Hydroperoxide (CAS No. 80-15-9), tert-butyl hydroperoxide (CAS No. 75-91-2), and tert-amyl hydroperoxide (CAS No. 3425-61-4), as well as the following azo compounds: 2,2'-azobis(isobutyronitrile) (CAS No. 78-671), 2,2'-azobis(2-methylbutyronitrile) (CAS No. 13472-08-7), and 1,1'azobis(1-cyclohexanenitrile) (CAS No. 2094-98-6).

[0036] The thermosetting catalyst may be an anionic curing agent, broadly described as an aza compound, amine compound, amide compound, imidazole compound, or combination thereof. More specific examples of aza compounds include the following: [ka]

[0037] More specific examples of amine compounds include aliphatic polyamines, aromatic polyamines, alicyclic polyamines, such as diethylenetriamine, triethylenetetraamine, diethylaminopropylamine, benzyldimethylamine, m-xylenediamine, diaminodiphenylamine, quinoxaline, isophoronediamine, mentendiamine, and combinations thereof.

[0038] More specific examples of amide compounds include functionalized amides and dicyandiamides.

[0039] More specific examples of imidazole compounds include isoimidazole, imidazole, 2-ethyl-4-methylimidazole, 2,4-dimethylimidazole, butylimidazole, 2-heptadecenyl-4-methylimidazole, 2-methylimidazole, 2-undecenylimidazole, 1-vinyl-2-methylimidazole, 2-undecylimidazole, 2-heptadecenylimidazole, 2-phenylimidazole, and 1-benzyl-2 -Methylimidazole, 1-propyl-2-methylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-guanaminoethyl-2-methylimidazole, addition products of imidazole and methylimidazole, addition products of imidazole and trimellitic acid, 2-n-hept Decyl-4-methylimidazole, phenylimidazole, benzylimidazole, 2-methyl-4,5-diphenylimidazole, 2,3,5-triphenylimidazole, 2-styrylimidazole, 1-(dodecylbenzyl)-2-methylimidazole, 2-(2-hydroxyl-4-t-butylphenyl)-4,5-diphenylimidazole, 2-(2-methoxyphenyl)-4,5-diphenylimidazole, 2-(3-hydroxy Examples include 4,5-diphenylimidazole (diphenyl)-4,5-diphenylimidazole, 2-(p-dimethylaminophenyl)-4,5-diphenylimidazole, 2-(2-hydroxyphenyl)-4,5-diphenylimidazole, di(4,5-diphenyl-2-imidazole)-benzene-1,4,2-naphthyl-4,5-diphenylimidazole, 1-benzyl-2-methylimidazole, 2-p-methoxystyrylimidazole, and combinations thereof.

[0040] Any additives In some embodiments, it may be desirable to add other additives to the conductive die-attach composition of the present invention. Examples of such additives include adhesion promoters, such as silanes, acids, and anhydrides.

[0041] In a preferred embodiment, a conductive die attach composition, A resin containing one or more maleimide, itaconimide, or nadiimide functional groups, or a combination of the said functional groups, wherein the resin contains one or more maleimide functional groups; An epoxy component, the epoxy component is selected from biphenyl epoxy resin, bisphenol A, E, S, or F epoxy resin, for example, bisphenol A epoxy resin; (Meth)acrylate component, said (meth)acrylate component is a mixture of a polyfunctional acrylate [e.g., Arkema's SR368 (trifunctional acrylate) and / or SR248 (neopentyl glycol dimethacrylate)] and a monofunctional (meth)acrylate [e.g., Arkema's SR506A (isobornyl acrylate)]; Aromatic anhydride, the aromatic anhydride being 4-methacryloxyethyl trimellitic anhydride; and A conductive filler, the conductive filler is silver. Includes.

[0042] In an alternative preferred embodiment, the conductive die attach composition is A resin comprising one or more maleimide, itaconimide, or nadiimide functional groups, or a combination thereof, wherein the resin contains one or more maleimide functional groups, present in an amount ranging from about 1% to about 10% by weight based on the total weight of the composition; The epoxy component, which is a bisphenol A epoxy resin, is present in an amount ranging from about 1% to about 5% by weight based on the total weight of the composition; (Meth)acrylate components, said (meth)acrylate components are mixtures of polyfunctional acrylates [e.g., Arkema's SR368 (trifunctional acrylate) and / or SR248 (neopentyl glycol dimethacrylate)] and monofunctional acrylates [e.g., Arkema's SR506A (isobornyl acrylate)], and combinations thereof, and are present in amounts ranging from about 1% to about 10% by weight based on the total weight of the composition; Aromatic anhydride, the aromatic anhydride being 4-methacryloxyethyl trimellitic anhydride, present in an amount ranging from about 0.1% to about 1% by weight based on the total weight of the composition; and A conductive filler, the conductive filler being silver, is present in an amount ranging from about 10% to about 90% by weight based on the total weight of the composition; Includes.

[0043] When cured by exposure to high-temperature conditions, the composition exhibits a die shear strength against a copper lead frame exceeding approximately 200% by weight compared to a comparative composition without aromatic anhydrides, after further exposure to high-temperature conditions of approximately 121°C and high humidity conditions of approximately 100% for approximately 16 hours.

[0044] This specification also provides methods for preparing such conductive die-attach compositions of the present invention, methods for using such conductive die-attach compositions of the present invention, methods for improving the adhesion of the conductive die-attach composition to a metal lead frame, and semiconductor devices formed using the conductive die-attach composition of the present invention.

[0045] In other words, the die attach composition of the present invention may be prepared by mixing the listed components and blending them to form a conductive die attach composition.

[0046] The die attach composition of the present invention may be applied to a substrate such as a circuit board or carrier substrate, a semiconductor chip or package may be placed on the applied die attach composition, and then exposed to conditions favorable for forming an adhesive bond between them.

[0047] The die attach composition of the present invention may also be used to improve the adhesion of a conductive die attach composition to a metal lead frame such as copper or nickel. The improvement effect observed by the formulation of the conductive die attach composition of the present invention is obtained, and this effect is thought to be brought about by the inclusion of aromatic anhydride. [Examples]

[0048] Example 1 Two types of resin systems were formulated: one containing methacryloxyethyl trimellitic anhydride ("4-META") and one without. Each formulation was prepared using the same components. That is, both formulations contained the components listed in Table 1, and one of them contained 0.25% by weight of 4-META.

[0049] [Table 1]

[0050] These formulations were used as die attach pastes applied to 3x3mm bare silicon dies with copper lead frames. Adhesion was measured by die shear strength ("DSS") at room temperature and 260°C using a Dage die shearing machine Series 4000. Six replicas were prepared using these two formulations and cured to a final temperature of 175°C over 30 minutes at a heating rate of 5°C per minute, after which the temperature was maintained in a nitrogen oven for approximately 30 minutes.

[0051] The post-cured parts were heated on a hot plate set to 240°C for approximately 1 minute, and then further baked in an oven at 175°C for 4 hours. These conditions were intended to mimic the wire bonding and molding process. Subsequently, the post-cured and molded samples were placed in a parbom chamber with distilled water, heated to approximately 121°C, and held for approximately 16 hours.

[0052] Subsequently, die shear tests were performed on the parts that had undergone this exposure treatment. The results shown in Table 2 below indicate that the die shear strength of post-cured and post-molded parts improved (by approximately 10-30%) in the formulation containing 0.25% 4-META, and after perbomb treatment, the die shear strength of both post-cured and post-molded cured parts improved significantly (by approximately 200-300%).

[0053] [Table 2]

[0054] Thus, the inclusion of 4-META improves the adhesion of the die attach paste on the copper lead frame and maintains strong die shear even after exposure to high temperature and humidity.

[0055] Example 2 Here, two types of die attach paste formulations were prepared: one without 4-META and one with 4-META. Each formulation was prepared using the same components; that is, both formulations contained the components listed in Table 3, one of which contained 0.46% by weight of 4-META. These formulations were used on nickel lead frames. [Table 3]

[0056] Each compound was placed on a 3x3 mm stainless steel die mounted on a nickel lead frame. The resulting assembly was cured on a hot plate set to 150°C for approximately 1 minute, then heated to 175°C in an oven over 30 minutes, and held in air for 30 minutes.

[0057] Die shear strength was measured at room temperature and 260°C using a Dage die shearing system series 4000. When 4-META content was between 0% and 0.46%, the die shear strength of the sample increased by 50%, and the die shear strength of the post-cured sample increased by 40%. When 4-META content was between 0% and 0.85%, the die shear strength of the sample increased by 10%, and the die shear strength of the post-cured sample increased by 20%.

[0058] [Table 4]

[0059] Thus, the inclusion of 4-META improved the adhesion of the die attach paste on the nickel lead frame and maintained strong die shear even after high-temperature exposure.

Claims

1. (a) A resin containing one or more maleimide, itaconimide, or nadiimide functional groups, or a combination of the said functional groups. (b) Epoxy components, (c) (meth)acrylate component, (d) aromatic anhydride, and (e) conductive filler, A conductive die attach composition containing the following:

2. The composition according to claim 1, wherein, when cured by exposure to high-temperature conditions, the composition exhibits a die shear strength against a copper lead frame of more than 200% by weight compared to a comparative composition without aromatic anhydrides after further exposure to high-temperature conditions of about 121°C and high humidity conditions of about 100% for about 16 hours.

3. The resin (a) is 【Chemistry 1】 (In the formula, m = 1 to 15, R is independently selected from hydrogen or alkyl groups having 1 to about 4 carbon atoms. X is a monovalent or polyvalent linkage containing an organic group or an organosiloxane group. The composition according to claim 1, which is a member selected from the group consisting of the following.

4. The composition according to claim 1, wherein the resin (a) is phenylenedimaleimide.

5. The composition according to claim 1, wherein the resin (a) is present in an amount of about 1% to about 10% by weight.

6. The composition according to claim 1, wherein the epoxy component (b) is a member selected from the group consisting of aromatic epoxy resins, aliphatic epoxy resins, and alicyclic epoxy resins.

7. The composition according to claim 1, wherein the epoxy component (b) is a member selected from the group consisting of biphenyl epoxy resin, bisphenol A, E, S, or F epoxy resin.

8. The composition according to claim 1, wherein the epoxy component (b) is present in an amount of about 0.5% to about 10% by weight.

9. The (meth)acrylate component (c) is H ２ C = CGCO ２ R １ Represented by the formula, where G is a member selected from the group consisting of H, halogens, and alkyl groups having 1 to about 4 carbon atoms, and R １ The composition according to claim 1, wherein is a member selected from the group consisting of alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkaryl, and aryl groups having 6 to about 16 carbon atoms, with or without substitution or interruption by a member selected from the group consisting of silane, silicon, oxygen, halogen, carbonyl, hydroxyl, ester, carboxylic acid, urea, urethane, carbamate, amine, amide, sulfur, sulfonate, and sulfone.

10. The (meth)acrylate component is silicone (meth)acrylate, polyethylene glycol di(meth)acrylate, tetrahydrofuran (meth)acrylate and di(meth)acrylate, hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, isobornyl acrylate, hexanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylenediglycol di(meth)acrylate, diglycerol tetra(meth)acrylate, tetramethylenedi(meth)acrylate The composition according to claim 1, which is a member selected from the group consisting of ester, ethylene di(meth)acrylate, neopentyl glycol di(meth)acrylate, butanediol di(meth)acrylate, bisphenol-A-(meth)acrylate, ethoxylated bisphenol-A-(meth)acrylate, bisphenol-F-(meth)acrylate, ethoxylated bisphenol-F-(meth)acrylate, bisphenol-A di(meth)acrylate, ethoxylated bisphenol-A-di(meth)acrylate, bisphenol-F-di(meth)acrylate, and ethoxylated bisphenol-F-di(meth)acrylate.

11. The composition according to claim 1, wherein the (meth)acrylate component (c) is a member selected from the group consisting of polyfunctional (meth)acrylates and monofunctional (meth)acrylates, and combinations thereof.

12. The composition according to claim 1, wherein the (meth)acrylate component (c) is present in an amount of about 1% to about 10% by weight.

13. The composition according to claim 1, wherein the aromatic anhydride (d) is a functionalized trimellitic anhydride.

14. The composition according to claim 1, wherein the aromatic anhydride (d) is 4-methacryloxyethyl trimellitic anhydride.

15. The composition according to claim 1, wherein the aromatic anhydride (d) is present in an amount of about 0.1% to about 1% by weight.

16. The composition according to claim 1, wherein the conductive filler (e) is silver powder or silver flakes.

17. The composition according to claim 1, wherein the conductive filler (e) is a combination of silver powder and silver flakes.

18. The conductive filler (e) is approximately 10 －７ ~about 10 －６ The composition according to claim 1, having particle sizes in the range of [specify particle size range].

19. The conductive filler (e) is approximately 10 －６ Silver powder having a particle size of, or about 10 －７ The composition according to claim 1, wherein the silver flakes have a particle size of [specified particle size].

20. The composition according to claim 1, wherein the conductive filler (e) is present in an amount of about 10% to about 90% by weight.

21. (a) A resin comprising one or more maleimide, itaconimide, or nadiimide functional groups, or a combination thereof, wherein the resin contains one or more maleimide functional groups. (b) Epoxy component, the epoxy component is a member selected from the group consisting of biphenyl epoxy resin, bisphenol A, E, S, or F epoxy resin. (c) (meth)acrylate component, the (meth)acrylate component is a mixture of polyfunctional (meth)acrylate and monofunctional (meth)acrylate, and combinations thereof. (d) Aromatic anhydride, the aromatic anhydride being 4-methacryloxyethyl trimellitic anhydride, and (e) Conductive filler, the conductive filler is silver. A conductive die attach composition containing [a specific component].

22. (a) A resin containing one or more maleimide, itaconimide, or nadiimide functional groups, or a combination of said functional groups, wherein the resin contains one or more maleimide functional groups, present in an amount ranging from about 1% by weight to about 10% by weight. (b) Epoxy component, the epoxy component is a bisphenol A epoxy resin, present in an amount ranging from about 1% by weight to about 5% by weight. (c) (meth)acrylate component, the (meth)acrylate component is a mixture of polyfunctional (meth)acrylate and monofunctional (meth)acrylate, and combinations thereof, present in an amount ranging from about 1% by weight to about 10% by weight. (d) Aromatic anhydride, the aromatic anhydride being 4-methacryloxyethyl trimellitic anhydride, present in an amount ranging from about 0.1% by weight to about 1% by weight, and (e) Conductive filler, the conductive filler is silver, present in an amount ranging from about 10% to about 90% by weight. A conductive die attach composition containing [a specific component].

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